6 Lessons Learned from Serial Entrepreneur Wayne Chang

As a founding member of Dropbox, Crashlytics, and now executive at Twitter, Wayne Chang has seen every aspect of a startup. He started his first company in his dorm room, pitched Dropbox to Y-Combinator, and exited Crashlytics with an acquisition by Twitter for a reported $259 Million. His talk Sunday at the University of Massachusetts at Amherst, was packed with stories and lessons learned from his career and life as an entrepreneur. Check out our top 6 lessons-learned from Chang’s talk.

Engineer Playfulness

“Playfulness is something that’s automatically endearing,” Chang stated during his talk Sunday. He went on to compare your startup to a friendly dog: giving your company that human feel makes users instantly want to interact with it. Chang explained that giving your users something unexpected and interesting in even the smallest of areas, like how Crashlytics does password recovery with fun and interactive graphics, makes users gravitate and cling to you as a startup.

Engineer Surprise

Everyone knows the story behind Tony Hsieh’s Zappos. Delivering Happiness: amazing customer service paired with truly amazing your customer when something goes wrong with their order. But Chang and Crashlytics have completely twisted this mindset. “That a really nice philosophy. It’s very ultra-reactive,” Chang explained during his talk, “If our whole entire philosophy is about building great relationships, why would I want to develop a relationship where the first thing they do is complain at me”. All this was based around opening up the conversation on a positive note and developing customer equity right from the start.

Develop the “Delta of Wow”

To stand out from the noise in busy startup spaces, Chang spoke extensively about the “Delta of Wow”. This delta shows the distance between you and your average competitor based off your ability to astound them with your product. The most critical step is finding the baseline of where your competitors are and what is the expected norm, then pointing out the places where your business can exceed them.

Generate Mystery

Before the launch of Crashlytics, the company set up its site allowing people to sign up for the service with only a description of the benefits of the product, without revealing any of the actual specs and features. To build up hype about the product, Crashlytics allowed bloggers and tech writers to get hands on with the product, telling them they could write only their impressions of the product, no screenshots or descriptions allowed. “So the developers are reading through and they’re like ‘What is this? They love it! But I don’t see any screenshots’”. All these pre-launch buzz generated a massive user basis for the company without them even seeing the product.

Keep It Gritty

Just months before the Twitter acquisition, Crashlytics moved to new office space in Boston in order to fit a growing team to develop their on-fire product. Chang described this move as not only necessary, but a total embodiment of his startup philosophy. “The worst thing that can happen to an entrepreneur is to think mentally that you’ve arrived, that you’re comfortable, that there’s no longer something worth striving for”. While personally designing the new space, Chang ordered glass panels for the conference room, running them $20,000 a piece, and a brand new Ikea conference table, tabbing in at $140. Chang talked about how much he loves this contrast between a totally polished look and something completely unfinished.

Be A Rock

During his very early startup days while still a student at the University of Massachusetts at Amherst, Chang began getting threats of legal action against his first company, i2Hub. One professor eased his nerves by saying “you can’t squeeze blood from a rock”, or that if you have nothing, you have nothing to lose. Be young and be risky and you’ll see the greatest outcomes.

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